My Last Sexual Experience

**I have been trying to keep up the habit of writing and posting every day. I ran out of things to review and my sex life has been a bit lacking, so I googled “sex blog writing prompts.” I came across a set of 10 questions and prompts that pertain to sex.**

2. Write about your last sexual experience. How was it different from your first sexual experience?

My last sexual experience was over two months ago. Andy came over and I cooked us dinner while we watched B-rated horror movies on Netflix. I wrote about it in stronger detail in the above link. We have been going through a bit of a dry spell at the moment. He has been busy with school, so he hasn’t been too focused on sex.

Anyways, to answer the question, there are a lot of differences between my first and last experiences. Back then I had no idea what I was doing. Now, I know exactly what I am doing and love to prolong my technique. I definitely have more experience and knowledge about sex and masturbation. I don’t feel as guilty after sexy encounters.

Both first and last encounters are different because of the partner. The partner I am currently with took things a lot slower than the first. The first shared many firsts with me, where my last and I don’t have very many firsts together, if any. In a way my first encounter was more special, but my last was way hotter. Both memories are fuzzy though, one was just because it was over 10 years ago, the other because I had consumed a lot of alcohol beforehand.

Cringeworthy

**This is not a sexy post. It is quite horrible actually, but I am writing it anyways just so that I can look back on what an idiot I was. Read at your own discretion.**

A few weeks ago on a Friday night I went to Andy’s after work. The plan was for us to go grocery shopping, cook dinner, and enjoy a night of video games and movies. We got about halfway through the list, but then I fucked up horribly.

I got drunk. Neither of us realized how much I really had until it was too late. I fell a lot. I told him I loved him for the first time. No, I didn’t just say that because I was drunk. I had plans of saying it before I even thought of alcohol that night. I just poorly misjudged his readiness. To his credit, he took it well, and apologized for not feeling the same way.

I don’t remember much of that night. I don’t remember how I told him, or when I did. I just know that I did. Then once I sobered up, I brought it up again and told him there was no pressure to say it back, that I just wanted him to know how I felt.

Sometime after telling him how I felt, I got sick all over his kitchen and bathroom. I fell some more. I was too drunk to clean it up myself and he had to do. I feel horrible, and I hate that I let myself get that inebriated that night.

He finally got me to scoot into the shower where I sat in the water. I don’t remember getting in the shower, but I have a small memory of finally being cleaned off and standing up, drying off.He finished the cleaning and brought me my overnight bag with pajamas and tooth brush.

We went to bed and I woke up with a hang over from hell and covered in bruises from falling so much. I still have a fucked up right shoulder. Every time we hang out now he will rub on it a bit, and it is finally starting to ease up on the pain. Unfortunately I had such a bad hangover that I couldn’t really go home until late Saturday night.

He says that that night doesn’t change how he feels about me, and he cares for me a lot. I am embarrassed that he had to see that and deal with that.

Punny

The other night while playing video games with the boyfriend I was having some difficulty fighting a “bad guy.” He commented that my attacks would work better if I hit from behind. I made a comment about the “bad guy” taking it up the ass.

From there the conversation turned to anal and I mentioned that my experience with it was….terrible. I then started laughing like a maniac because the word I almost used was “shitty.” I then told him what I was about to say.

We both had a good laugh at my terrible pun.

Thirst

We might have had a little bit too much wine, and I had to work the next morning. I didn’t care, and figured I could catch up on sleep the next night. All I wanted was to enjoy a night in with Andy. 

I cooked him dinner and we watched B-rated horror movies on netflix. The movies were terrible, but we had a blast adding our own commentary to the films. 

The first bottle of wine was drained fast. He convinced me to open the other. We drank that even faster. At one point my hand began resting on the crotch of his pants. I began to rub, feeling his hardness grow immediately. He inquired about my roommate being home, and I quickly shrugged it off. I could behave if she came out of her room, though I was pretty certain she would make herself scarce.

Eventually my hand worked itself into his shorts and I got a nice grip on his shaft. I twirled my index finger around the head, lingering on the frenulum where I did small, light circles. 

With his right arm around my shoulders and his left hand gently stroking my face and hand, I somehow manuevered my mouth onto his thumb. I began treating it like I would his cock; swirling, sucking, and massaging it with my tongue. His moans were steadily getting louder. 

Unable to take the teasing, he removed his thumb from my mouth and reached down to unzip. His cock was finally free, so I lowered my head and started by kissing his head. Slowly I lowered my mouth, covering the whole head. Swirling my tongue and sucking, I began to bob my head up and down. I had a terrible angle, so I was only able to attend to his head. 

I don’t remember much (or most) of the movie, but I do remember telling him at one point that the movie needed to end so we could go to my room. I don’t remember if we finished the movie, but eventually we landed in my room. 

After shutting the door, I flipped back the top blanket and walked around to the side that gives me the best cock sucking angle. By the time I got to my side, he was on my bed naked and waiting. 

To be continued…

Preparation

I came to the realization the other day that everyone I have ever dated has prepared me for Andy. So far Andy is my favorite boyfriend That I have ever had, the best one I ever dated, etc.

The biggest example I can think of is J. Andy and J are similar in the fact that they both have major ups and downs. The only difference is that Andy hasn’t done anything to disappoint me (knock on wood). J was infamous for flaking on all the time, however, Andy has only had to cancel once, and that was due to homework. School comes first, I get it. Totally excusable. J just flaked because he could, didn’t care how I felt, etc.They both have severe mood swings, and I saw the worst of J. In the end I realized he was controlling in his passive aggressiveness. I have yet to see the darker side of Andy, granted, but I know it is there and feel prepared in how to deal thanks to my experience with J.,

Another example would be Will. If I hadn’t had the experience of slow moving Will, I would have given up on Andy way too soon. Yes, there were many mixed signals, but mostly good ones that kept me encouraged to keep pursuing Andy.

As far as Lee goes, Andy graduates next semester. Lee left easily, without looking back. I know that a lot can happen in 5 or 6 months, but in that time Andy will be graduating. I have been having to think about whether I could drop everything and move (if that’s what his future prospects require him to do, or if I could handle long distance, or if we even need to break things off.

As far as H goes, he broke down my most recent wall. I was made vulnerable again, allowing myself to open up to Andy enough to let him in and in the end take the next step of boyfriend and girlfriend.

There were many others in between, but those are the ones with the most significant impact on me, allowing me to be ready for everything that Andy has to offer, plus so much more.The good, the bad, and the ugly.

Sneaky Fondle

It was getting late and I was ready to go back to his place. We were at my coworker’s place, where we had just wrapped up the board game we were playing. My coworker went to bed, leaving her husband to chat and visit with Andy and I. 

I snuggled next to Andy on the couch and he wrapped his left arm around me while holding my right hand with his, my arm stretched out across his lap. 

Coworker’s husband (we’ll call him CH) was setting up his new console while chatting with Andy, not paying too much attention to us. 

I began to run my hand up and down his thigh (not too far so as to be inappropriate, but enough to hint that I wanted to touch him). Still holding my hand, he surprised me by sliding it under his shorts, resting just shy of his cock. He released my hand and pulled his shorts down to cover my hand. 

They talked while I explored. I had a bad angle, so I wasn’t able to weild his dick in my hand. I was however, able to run my finger along the tip and up and down the shaft. 

I was feeling naughty and ready to play. To be honest, I had been ready all afternoon, but had behaved myself until now. He started to get hard and finally asked the magic question of if I was ready to go. 

CH was busy with his new game and hadn’t even noticed what I was up to. I slid my hand out of his shorts and stood up. Andy stood up after giving himself a slight adjustment. We gathered our things as we said goodbye and walked back to my car.

On the way back to Andy’s I gethered my courage and asked if he was up for a little fun before I had to get home. You know his answer was yes.  

From Baby Steps to Doing it All

I made sure to get off work early so that I had sufficient time to get ready for Andy to come over for dinner. I did some last minute cleaning and a quick shower before I started on dinner. I started to get a little concerned when I hadn’t heard from him by the time dinner was just about done. Finally he texted, but after the time we had scheduled. He over slept and was on his way.

After driving to 3 different places for wine, he finally showed up 2 hours later. I would have been annoyed, but I was just glad he didn’t cancel like everyone else would have. We watched some of the anime he loaned me while we ate. Eventually my roommate came out to cook her dinner, but thankfully kept to herself. After she was done cooking, she left us to go to her friend’s.

We finished the anime and decided to go play my Super Nintendo. We chose Donkey Kong, one of our child hood favorites. We  did pretty good at first, but the wine snuck up on us and we kept dying. After dying for what felt like the twentieth time on my favorite level, I tossed the remote aside and leaned over him smiling. I leaned a little closer and we kissed. One kiss turned into three, then I lost count as we began to make out.

The background music of the game got irritating after a while, so we stopped kissing long enough to turn it off. As soon as it was off, we went right back to kissing, this time clothing was getting removed. There was a lot of heavy petting, and eventually he was delighted to have found my nipple piercings.

Soon we were naked and I told him where my condoms were, as he had my pinned down. The sex was good and hot. It was rough than I had ever experienced, but I found it thrilling and exciting. My chest and neck are covered in hickeys and bruises, a nice reminder of the other night.

After sex, we hopped in the shower and rinsed off our sweaty and hot bodies. We kissed and nibbled some more.

Once out of the shower we got dressed and cuddled on my bed talking. I gathered up the courage and asked what we were, asking if he considered us boyfriend and girlfriend. I was happy to hear him say yes, that neither of us do friends with benefits.

I was up 24 hours by the time I got in bed that morning, but it was well worth it. The next night I hung out at his place for a few hours before he had to go to bed. He cooked dinner again and we had some fresh brownies. I probably won’t see him until after this is posted. I am excited to see where this goes.

It Comes in Twos

One thing I have noticed recently is that my dating life tends to come in twos. Anytime I have got into some kind of relationship, it has always been when I had to choose between one guy and another.

Example 1: Right before Ex #3 and I became an item my mom was trying to set me up with a Fireman she met at her work. He picked me up once and we hung out. I started seeing Ex #3 right after so things never progressed. I really wish I remembered more about my time with the firefighter because that would have been a decent post, being as how most every female has a fireman fantasy. Damn I missed out on that one!

Example 2: Right before I started seeing Will, I had a huge Crush on Brent. It was a huge toss up on which one would make a move first. In the end Will made the first move, which I think in the end was best because I honestly don’t think Brent and I would have worked in the end because of religious differences. Well, Will and I didn’t work out for other reasons, but that’s not the point.

Example 3:  Any minor relationship that comes about, J comes back into the picture. Something usually happens to end things with said new guy to make me end up with J. J then burns me a little bit more by disappearing himself.

Example 4 – The Present: At the beginning of October I started talking to a guy on a dating site. We had a lot in common and talked online for over a month. After the month was up I asked if he wanted to meet. We had lunch and things went well. We exchanged numbers and texted often. I was honestly surprised he stayed talking to me, since I don’t have the best track record when it comes to that. I will call him Andy.

Not even after a week of meeting Andy, A guy I will call H texts me out of the blue and asks me to go to a concert. To make up for having to drive the opposite direction I say he can buy dinner since I don’t accept gas money. At the end we decide it is a date.

All week I think about how it always comes in twos. I was worried about who I should choose, wondering if at least one will stick around to be my date to my work’s Christmas party. I didn’t want to lead either of them on or have one of them end up getting hurt. I think I have decided on who has the most potential, but that will be another post.

The Right One

I learned a very valuable lesson with the last guy I dated, however I just now realized it. I learned why people say they will “try something with the right person.”

We all have fantasies. Some are more kinky than others. Some of my fantasies are on the kinkier side. The guy I dated wanted to know them. I was embarrassed, but I shyly told him. He wasn’t disgusted, but he wasn’t into it either. I dropped it.

However, he always ended up bringing it up. He offered to try those things with me. I wasn’t really excited to, but I did try because I worried no one else would offer. I figured I was just nervous to, and I was deep down, but it was more than that.

I wasn’t as into it. I mean, the idea still turned me on, I still got off watching it on porn, but with him it felt wrong. I realize now it is because he just wasn’t the right one. Even though he was trying to be the nice, supportive boyfriend, I couldn’t get into it because he wasn’t into it as sexually as I was. That is why I was so uncomfortable.

I know now the true meaning of waiting for the right one. I need to try these things with someone that gets off on doing the things for me, not just doing me a favor.

Relationship and a Half (Part 2)

About a month after the last guy, I met someone on a dating website. We had a bunch in common, and seemed to have a lot to talk about. We met after a week of talking. I had my mom drop me off at a gas station near his place and we walked there. We watched a bit of netflix and cuddled, ate some of his homemade pizza and played video games. Towards the end he kissed me. I liked the way he kissed, so I kissed back and we had a nice make out session.

Over the next couple of weeks it felt like we had amazing chemistry. We communicated well, never really fighting or arguing. We didn’t really have problems until the second week or so when we had our first sleep over. The guy talked like he had a huge sex drive and promised a weekend of sex. It was my dream come true.

However, that first night when we went to bed was full of disappointment. He got me incredibly turned on. He was riding me hard then I just got the feeling like something was wrong. He stopped not long after to say he just wasn’t feeling it and apologized. I was like , “What the fuck?”

We got dressed and went to the living room. He then told me that I reminded him of his mother and he just wasn’t attracted to me, blondes in particular. He then had the nerve to ask if I would dye my hair, and maybe that would help. Pathetically I agreed. I should have dumped him then.

The next day I went with my roommate to go get hair dye and she dyed my hair. He loved it, but I just didn’t trust him anymore. I always felt like he wasn’t that into me, he was only into the idea of me.

There were other warning signs that he was not the one for me. He refused to work and lived off the system, claiming to take care of his roommate. His roommate was a girl he used to be friends with benefits with. He also never calmed me sexy, pretty, beautiful, or hot. However, he always described other girls this way.

One night the discussion of politics came up. I avoided it and he got offended. He kept prodding and badgering about my views, which i refused to give. He got very upset, feeling like I was hiding something from him. I finally told him my views, and he told me why I was wrong.

The last month we were together we never had sex. I tried, and it just didn’t happen. When I asked about it, he said we could try. We tried, and failed. Every time he started to bring his dick near my pussy he lost his boner. It was hard not to feel like it was me.

We started dating in July and broke up at the end of September when I went back to work. I hated him for sitting on his ass doing nothing when I worked my ass off every day. It didn’t help that J decided to start messaging me after nearly 6 months of silence.

I borrowed my roommate’s car that September night and went over to “the boyfriend’s” place. We talked and I told him it was over. I was nice about it. I told him I needed to work on me, and we both just weren’t in a situation where were good together. It was like a huge weight was lifted off my shoulders. I told him we could stay friends, and for the most part we have, though I kind of want nothing to do with him.